Lithium Hydroxide → HCID 67486669, compound

HRID 1755180Notes

Reaction equation

HRID 1755180 reaction equation
C[O:2][C:3](=[O:43])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:25](=[O:42])[N:26]([C:33]2[O:41][C:37]3=[CH:38][CH:39]=[CH:40][C:36]3=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]=3)=[CH:15][CH:14]=2)=[CH:6][CH:5]=1.[OH-].[Li+]>C1COCC1.CO.O>[O:41]1[C:37]2=[CH:38][CH:39]=[CH:40][C:36]2=[CH:35][CH:34]=[C:33]1[N:26]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:25]([CH:11]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]=2)=[CH:17][CH:18]=1)[CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:43])=[O:2])=[CH:5][CH:6]=1)=[O:42]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68181124HCID 68181124, compound

Product 1

HCID 67486669HCID 67486669, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To the crude 4-[2-(4-Benzofuran-2-ylphenylcarbamoyl)-3-(4-cyclohex-1-enylphenyl)-propyl]-benzoic acid methyl ester from step e dissolved in 20 mL of THF/MeOH/H2O (3:1:1) was added lithium hydroxide (74 mg, 1.8 mmol) After stirring for 5 hrs at RT, the organic solvents were removed under vacuum and the reaction residue diluted further with water (25 mL). The aqueous mixture was made acidic with 1 N HCl and extracted with ethyl acetate. The ethyl acetate portion was then dried over Na2SO4 and concentrated under vacuum to afford 4-[2-(4-Benzofuran-2-ylphenylcarbamoyl)-3-(4-cyclohex-1-enylphenyl)-propyl]-benzoic acid which was carried on as is for the next step.

Workup

  1. customthe organic solvents were removed under vacuum
  2. additionthe reaction residue diluted further with water (25 mL)
  3. extractionextracted with ethyl acetate
  4. dry with materialThe ethyl acetate portion was then dried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c1763a61d54d488191120e97d7a797d8
Source dataset
uspto-grants-2015_10
Patent number
US09169201B2

Reaction notes

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